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Oxyphenbutazone

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Chemical compound
Pharmaceutical compound
Oxyphenbutazone
Clinical data
Trade names Tandearil, Tanderil
AHFS/Drugs.com International Drug Names
ATC code
Legal status
Legal status
  • AU: Withdrawn
  • UK: Withdrawn
  • US: Withdrawn
Identifiers
  • (RS)-4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.004.489 Edit this at Wikidata
Chemical and physical data
Formula C19H20N2O3
Molar mass 324.380 g·mol−1
3D model (JSmol)
Chirality Racemic mixture
  • O=C2N(c1ccc(O)cc1)N(C(=O)C2CCCC)c3ccccc3.O
  • InChI=1S/C19H20N2O3.H2O/c1-2-3-9-17-18(23)20(14-7-5-4-6-8-14)21(19(17)24)15-10-12-16(22)13-11-15;/h4-8,10-13,17,22H,2-3,9H2,1H3;1H2 checkY
  • Key:CNDQSXOVEQXJOE-UHFFFAOYSA-N checkY
 NcheckY (what is this?)   (verify)

Oxyphenbutazone is a nonsteroidal anti-inflammatory drug (NSAID).[1] It is a metabolite of phenylbutazone.[2]

It was withdrawn from markets worldwide in mid-1980s due to bone marrow suppression and the risk of Stevens–Johnson syndrome.[3] [4]

In Scrabble , the word "oxyphenbutazone" is the present highest scoring word resulting in 1,780 points based on the NASPA word list of 2006.[5]

References

[edit ]
  1. ^ Singh N, Jabeen T, Somvanshi RK, Sharma S, Dey S, Singh TP (November 2004). "Phospholipase A2 as a target protein for nonsteroidal anti-inflammatory drugs (NSAIDS): crystal structure of the complex formed between phospholipase A2 and oxyphenbutazone at 1.6 A resolution". Biochemistry. 43 (46): 14577–83. doi:10.1021/bi0483561. PMID 15544328.
  2. ^ Matthews NS, Peck KE, Taylor TS, Mealey KL (May 2001). "Pharmacokinetics of phenylbutazone and its metabolite oxyphenbutazone in miniature donkeys". American Journal of Veterinary Research. 62 (5): 673–5. doi:10.2460/ajvr.200162673 . PMID 11341383.
  3. ^ Fung M, Thornton A, Mybeck K, Wu JH, Hornbuckle K, Muniz E (January 2001). "Evaluation of the Characteristics of Safety Withdrawal of Prescription Drugs from Worldwide Pharmaceutical Markets-1960 to 1999". Therapeutic Innovation & Regulatory Science. 35 (1): 293–317. doi:10.1177/009286150103500134. S2CID 73036562.
  4. ^ Biron P (May 1986). "Withdrawal of oxyphenbutazone: what about phenylbutazone?". CMAJ. 134 (10): 1119–20. PMC 1491052 . PMID 3697857.
  5. ^ Wood D (22 May 2008). "Record for the Highest Scoring Scrabble Move". Scrabulizer. Archived from the original on 11 May 2023.
Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones /
pyrazolidines
salicylates
acetic acid derivatives
and related substances
oxicams
propionic acid
derivatives (profens)
n-arylanthranilic
acids (fenamates)
COX-2 inhibitors
(coxibs)
other
NSAID
combinations
Key: underline indicates initially developed first-in-class compound of specific group; #WHO-Essential Medicines; withdrawn drugs; veterinary use.


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